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The ether extract is then dried over potassium carbonate and
the ether removed by distillation on the water-bath. The
phenyl methyl carbinol which remains is distilled under reduced
pressure; b. p. 100 at 15 mm. ; IIO~IIIQ at 28 mm. ; 118 at
40 mm. Yield, 20 grams.

The same method may be used without modification for pre-
paring phenyl ethyl carbinol using a corresponding quantity of
ethyl iodide. See Appendix^ p. 307.

Benzoyl Chloride, C0H5CO.C1

Wohler, AnnaJen, 1832, 3, 262 ; Cahours, Annalcn, 1846, 60,

28 grms. benzoic acid.

50        phosphorous pentachloride.

A round flask (250 c.c.) is fitted with an air-condenser. The
phosphorous pentachloride is introduced from the bottle and
weighed by difference. The operation must be conducted in
the fume-cupboard. The benzoic acid is then added, and the
air-condenser attached to the flask.* The action begins almost
immediately, and clouds of hydrochloric fumes are evolved.
The whole contents become liquid and consist of benzoyl
chloride (b. p. 200), phosphorous oxychloride (b. p. 107), and
unchanged pentachloride. Most of the oxychloride may be
removed by distilling in vacua on the water-bath. The re-
mainder is fractionated at the ordinary pressure and collected at
190-200. Yield, 20 25 grams.

Properties.  Colourless liquid, which fumes in the air and
possesses a pungent smell ; b. p. 198*5 ; sp. gr. 1*214 at 19.

Reactions.  i. Add a few drops of benzoyl chloride to i c.c. of
water ; the benzoyl chloride does not decompose at once, and
requires warming for some time before it is completely dissolved
(compare acetyl chloride, p. 74).

2. Add 2 c.c. ethyl alcohol to i c.c. benzoyl chloride and
caustic soda solution until alkaline, and warm gently. After a
time the smell of benzoyl chloride disappears, and ethyl benzoate